IL103156A - Process for the preparation of anti-ulcer pyridylmethyl sulfinyl benzimidazole derivatives - Google Patents
Process for the preparation of anti-ulcer pyridylmethyl sulfinyl benzimidazole derivativesInfo
- Publication number
- IL103156A IL103156A IL10315692A IL10315692A IL103156A IL 103156 A IL103156 A IL 103156A IL 10315692 A IL10315692 A IL 10315692A IL 10315692 A IL10315692 A IL 10315692A IL 103156 A IL103156 A IL 103156A
- Authority
- IL
- Israel
- Prior art keywords
- ulcer
- preparation
- benzimidazole derivatives
- bridge
- sulfinyl benzimidazole
- Prior art date
Links
- HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical class N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 title 1
- 230000000767 anti-ulcer Effects 0.000 title 1
- 239000002904 solvent Substances 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003699 antiulcer agent Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Compounds Of Unknown Constitution (AREA)
Abstract
Anti-ulcer agents having a methylsulfinyl bridge between a substituted pyridine moiety and a substituted benzimidazole moiety are prepared by oxidizing the corresponding compounds, having a methylthio bridge, with magnesium monoperoxyphthalate in a suitable solvent. The reaction may be run in an aromatic hydrocarbon solvent, wherein the product may crystallize out of the reaction solution and may be directly isolated by filtration.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76456491A | 1991-09-20 | 1991-09-20 | |
| US77787391A | 1991-10-15 | 1991-10-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL103156A0 IL103156A0 (en) | 1993-02-21 |
| IL103156A true IL103156A (en) | 1997-02-18 |
Family
ID=27117485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10315692A IL103156A (en) | 1991-09-20 | 1992-09-14 | Process for the preparation of anti-ulcer pyridylmethyl sulfinyl benzimidazole derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5391752A (en) |
| EP (1) | EP0533264B1 (en) |
| JP (1) | JPH0720956B2 (en) |
| KR (1) | KR100242622B1 (en) |
| CN (1) | CN1048729C (en) |
| AT (1) | ATE186535T1 (en) |
| AU (1) | AU649355B2 (en) |
| CA (1) | CA2078517C (en) |
| DE (1) | DE69230278T2 (en) |
| DK (1) | DK0533264T3 (en) |
| ES (1) | ES2143468T3 (en) |
| GR (1) | GR3032619T3 (en) |
| IL (1) | IL103156A (en) |
| MX (1) | MX9205333A (en) |
| NZ (1) | NZ244301A (en) |
| PT (1) | PT533264E (en) |
| WO (1) | WO1993006097A1 (en) |
| YU (1) | YU48291B (en) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9002043D0 (en) * | 1990-06-07 | 1990-06-07 | Astra Ab | IMPROVED METHOD FOR SYNTHESIS |
| US5504082A (en) * | 1992-06-01 | 1996-04-02 | Yoshitomi Pharmaceutical Industries, Ltd. | Pyridine compound and pharmaceutical compostions |
| KR950701921A (en) * | 1992-06-01 | 1995-05-17 | 고야 다다시 | Pyridine Compound and its Pharmaceutical Use (PYRIDINE COMPOUND AND MEDICINAL USE THEREOF) |
| SE521100C2 (en) * | 1995-12-15 | 2003-09-30 | Astra Ab | Process for the preparation of a benzimidazole compound |
| US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
| US6489346B1 (en) * | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US6699885B2 (en) * | 1996-01-04 | 2004-03-02 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and methods of using same |
| US6645988B2 (en) | 1996-01-04 | 2003-11-11 | Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| CN1053444C (en) * | 1996-03-20 | 2000-06-14 | 常州市第四制药厂 | Process for refining omeprazole |
| SE508669C2 (en) * | 1996-04-26 | 1998-10-26 | Astra Ab | New procedure |
| SK283805B6 (en) * | 1996-09-09 | 2004-02-03 | Slovakofarma, A. S. | Method of omeprazole preparation |
| SE9704183D0 (en) | 1997-11-14 | 1997-11-14 | Astra Ab | New process |
| US6166213A (en) * | 1998-08-11 | 2000-12-26 | Merck & Co., Inc. | Omeprazole process and compositions thereof |
| US6191148B1 (en) | 1998-08-11 | 2001-02-20 | Merck & Co., Inc. | Omerazole process and compositions thereof |
| US6852739B1 (en) | 1999-02-26 | 2005-02-08 | Nitromed Inc. | Methods using proton pump inhibitors and nitric oxide donors |
| US6245913B1 (en) | 1999-06-30 | 2001-06-12 | Wockhardt Europe Limited | Synthetic procedure for 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methylthio]-IH-benzimidazole hydrochloride and its conversion to omeprazole |
| US6268385B1 (en) | 1999-08-26 | 2001-07-31 | Robert R. Whittle | Dry blend pharmaceutical formulations |
| US6312723B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Pharmaceutical unit dosage form |
| US6369087B1 (en) | 1999-08-26 | 2002-04-09 | Robert R. Whittle | Alkoxy substituted benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6316020B1 (en) | 1999-08-26 | 2001-11-13 | Robert R. Whittle | Pharmaceutical formulations |
| US6780880B1 (en) | 1999-08-26 | 2004-08-24 | Robert R. Whittle | FT-Raman spectroscopic measurement |
| US6262085B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Alkoxy substituted Benzimidazole compounds, pharmaceutical preparations containing the same, and methods of using the same |
| US6326384B1 (en) | 1999-08-26 | 2001-12-04 | Robert R. Whittle | Dry blend pharmaceutical unit dosage form |
| US6312712B1 (en) | 1999-08-26 | 2001-11-06 | Robert R. Whittle | Method of improving bioavailability |
| US6262086B1 (en) | 1999-08-26 | 2001-07-17 | Robert R. Whittle | Pharmaceutical unit dosage form |
| DE19951960C2 (en) | 1999-10-28 | 2002-06-27 | Gruenenthal Gmbh | Process for the preparation of benzimidazole derivatives suitable as ulcer therapeutics |
| PL368563A1 (en) * | 2001-02-02 | 2005-04-04 | Teva Pharmaceutical Industries Ltd. | Processes for the production of substituted 2-(2-pyridylmethyl) sulfinyl-1h-benzimidazoles |
| KR100783020B1 (en) * | 2001-03-23 | 2007-12-07 | 동아제약주식회사 | 2-Methylchloride Pyridine Derivative and Preparation Method of Benzimidazole Derivative Using the Same |
| EP1409478B1 (en) * | 2001-07-16 | 2006-03-29 | Janssen Pharmaceutica N.V. | Improved process for preparing benzimidazole-type compounds |
| US20040006111A1 (en) * | 2002-01-25 | 2004-01-08 | Kenneth Widder | Transmucosal delivery of proton pump inhibitors |
| WO2004012659A2 (en) * | 2002-08-01 | 2004-02-12 | Nitromed, Inc. | Nitrosated proton pump inhibitors, compositions and methods of use |
| SE0203092D0 (en) * | 2002-10-18 | 2002-10-18 | Astrazeneca Ab | Method for the synthesis of a benzimidazole compound |
| US7507829B2 (en) | 2002-12-19 | 2009-03-24 | Teva Pharmaceuticals Industries, Ltd | Solid states of pantoprazole sodium, processes for preparing them and processes for preparing known pantoprazole sodium hydrates |
| ES2324665T3 (en) * | 2003-01-15 | 2009-08-12 | Cipla Limited | PHARMACEUTICAL PROCESS AND COMPOUNDS PREPARED THROUGH THE SAME. |
| US20040248942A1 (en) * | 2003-02-20 | 2004-12-09 | Bonnie Hepburn | Novel formulation, omeprazole antacid complex-immediate release for rapid and sustained suppression of gastric acid |
| WO2004080961A2 (en) * | 2003-03-12 | 2004-09-23 | Teva Pharmaceutical Industries Ltd. | Crystalline and amorphous solids of pantoprazole and processes for their preparation |
| US7683177B2 (en) | 2003-06-10 | 2010-03-23 | Teva Pharmaceutical Industries Ltd | Process for preparing 2-[(pyridinyl)methyl]sulfinyl-substituted benzimidazoles and novel chlorinated derivatives of pantoprazole |
| WO2005007117A2 (en) * | 2003-07-18 | 2005-01-27 | Santarus, Inc. | Pharmaceutical formulation and method for treating acid-caused gastrointestinal disorders |
| US8993599B2 (en) * | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| CA2531564C (en) * | 2003-07-18 | 2016-01-19 | Santarus, Inc. | Pharmaceutical composition for inhibiting acid secretion |
| US20070292498A1 (en) * | 2003-11-05 | 2007-12-20 | Warren Hall | Combinations of proton pump inhibitors, sleep aids, buffers and pain relievers |
| CA2563808A1 (en) * | 2004-04-28 | 2005-11-10 | Altana Pharma Ag | Dialkoxy-imidazopyridines derivatives |
| US8906940B2 (en) * | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US8815916B2 (en) * | 2004-05-25 | 2014-08-26 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| CN103121992A (en) * | 2004-06-24 | 2013-05-29 | 阿斯利康(瑞典)有限公司 | New process for the preparation of crystal modifications for use in the preparation of esomeprazole sodium salt |
| GB0525710D0 (en) * | 2005-12-17 | 2006-01-25 | Pliva Hrvatska D O O | An improved process for preparing of substituted 2-benzimidazolesulfoxide compounds |
| WO2008017020A2 (en) * | 2006-08-03 | 2008-02-07 | Dr. Reddy's Laboratories Limited | Process for preparing proton pump inhibitors |
| US20090092658A1 (en) * | 2007-10-05 | 2009-04-09 | Santarus, Inc. | Novel formulations of proton pump inhibitors and methods of using these formulations |
| EA200900985A1 (en) | 2007-01-31 | 2009-12-30 | Крка, Товарна Здравил, Д. Д., Ново Место | METHOD OF OBTAINING OPTICAL PURE OMEPRAZOL |
| WO2010134099A1 (en) | 2009-05-21 | 2010-11-25 | Cadila Healthcare Limited | One pot process for preparing omeprazole and related compounds |
| CN104203938A (en) | 2012-01-21 | 2014-12-10 | 朱比兰特生命科学有限公司 | Process for the preparation of 2-pyridylmethylsulfinylbenzimidazoles, their analogs and optically active enantiomers |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7804231L (en) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Gastric acid secretion |
| US4483781A (en) * | 1983-09-02 | 1984-11-20 | The Procter & Gamble Company | Magnesium salts of peroxycarboxylic acids |
| JPS6150978A (en) * | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | Pyridine derivative and preparation thereof |
| JPS61178919A (en) * | 1985-02-04 | 1986-08-11 | Banyu Pharmaceut Co Ltd | Benzimidazole derivative and drug containing same |
| JPS62201884A (en) * | 1986-02-28 | 1987-09-05 | Tokyo Tanabe Co Ltd | Benzimidazole derivative |
| JPH0643426B2 (en) * | 1986-07-25 | 1994-06-08 | 東京田辺製薬株式会社 | Imidazo [4,5-b] pyridine derivative, method for producing the same, and antiulcer agent containing the same |
| FI864046A7 (en) * | 1986-10-07 | 1988-04-08 | Farmos Oy | Method for preparing a therapeutically active compound. |
| FI90544C (en) * | 1986-11-13 | 1994-02-25 | Eisai Co Ltd | Process for Preparation as Drug Useful 2-Pyridin-2-yl-methylthio- and sulfinyl-1H-benzimidazole derivatives |
| DE3722810A1 (en) * | 1987-07-10 | 1989-01-19 | Hoechst Ag | SUBSTITUTED BENZIMIDAZOLES, METHOD FOR THE PRODUCTION THEREOF, THE PHARMACEUTICAL PREPARATIONS CONTAINING THEM AND THE USE THEREOF |
| DK171989B1 (en) * | 1987-08-04 | 1997-09-08 | Takeda Chemical Industries Ltd | Process for the preparation of 2- (2-pyridylmethylsulfinyl) benzimidazoles |
| WO1989005299A1 (en) * | 1987-12-11 | 1989-06-15 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Novel benzimidazole derivatives |
| SE8804628D0 (en) * | 1988-12-22 | 1988-12-22 | Ab Haessle | NEW COMPOUNDS |
| SE8804629D0 (en) * | 1988-12-22 | 1988-12-22 | Ab Haessle | NEW THERAPEUTICALLY ACTIVE COMPOUNDS |
| FR2660313B1 (en) * | 1990-04-02 | 1992-07-03 | Fournier Ind & Sante | NEW SULFONYL-PHENYL-BETHA-D-THIOXYLOSIDES, THEIR PREPARATION PROCESS AND THEIR USE IN THERAPEUTICS. |
-
1992
- 1992-09-11 WO PCT/US1992/007712 patent/WO1993006097A1/en not_active Ceased
- 1992-09-11 NZ NZ244301A patent/NZ244301A/en not_active IP Right Cessation
- 1992-09-12 ES ES92202792T patent/ES2143468T3/en not_active Expired - Lifetime
- 1992-09-12 EP EP92202792A patent/EP0533264B1/en not_active Expired - Lifetime
- 1992-09-12 DK DK92202792T patent/DK0533264T3/en active
- 1992-09-12 AT AT92202792T patent/ATE186535T1/en not_active IP Right Cessation
- 1992-09-12 PT PT92202792T patent/PT533264E/en unknown
- 1992-09-12 DE DE69230278T patent/DE69230278T2/en not_active Expired - Fee Related
- 1992-09-14 JP JP4244822A patent/JPH0720956B2/en not_active Expired - Fee Related
- 1992-09-14 IL IL10315692A patent/IL103156A/en not_active IP Right Cessation
- 1992-09-17 CA CA002078517A patent/CA2078517C/en not_active Expired - Fee Related
- 1992-09-18 KR KR1019920016990A patent/KR100242622B1/en not_active Expired - Fee Related
- 1992-09-18 MX MX9205333A patent/MX9205333A/en not_active IP Right Cessation
- 1992-09-18 AU AU25207/92A patent/AU649355B2/en not_active Ceased
- 1992-09-19 CN CN92110899A patent/CN1048729C/en not_active Expired - Fee Related
- 1992-10-07 YU YU89492A patent/YU48291B/en unknown
-
1993
- 1993-02-22 US US08/022,804 patent/US5391752A/en not_active Expired - Lifetime
-
2000
- 2000-02-09 GR GR20000400318T patent/GR3032619T3/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69230278T2 (en) | 2001-04-05 |
| AU2520792A (en) | 1993-03-25 |
| EP0533264B1 (en) | 1999-11-10 |
| CN1048729C (en) | 2000-01-26 |
| DE69230278D1 (en) | 1999-12-16 |
| NZ244301A (en) | 1994-08-26 |
| JPH0720956B2 (en) | 1995-03-08 |
| PT533264E (en) | 2000-05-31 |
| IL103156A0 (en) | 1993-02-21 |
| MX9205333A (en) | 1993-07-01 |
| ES2143468T3 (en) | 2000-05-16 |
| KR100242622B1 (en) | 2000-03-02 |
| DK0533264T3 (en) | 2000-05-15 |
| ATE186535T1 (en) | 1999-11-15 |
| US5391752A (en) | 1995-02-21 |
| WO1993006097A1 (en) | 1993-04-01 |
| JPH05213936A (en) | 1993-08-24 |
| AU649355B2 (en) | 1994-05-19 |
| CA2078517A1 (en) | 1993-03-21 |
| EP0533264A1 (en) | 1993-03-24 |
| GR3032619T3 (en) | 2000-05-31 |
| YU48291B (en) | 1998-05-15 |
| KR930006021A (en) | 1993-04-20 |
| YU89492A (en) | 1995-10-03 |
| CN1071169A (en) | 1993-04-21 |
| CA2078517C (en) | 2003-11-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |